Holly Sampson Undercover

Holly Sampson, one of several women, who have now claimed they have had sexual affairs with embattled golfer Tiger Woods, appears to have a complicated past with legal implications. Sampson, a 36-year-old lingerie model and porn star, appears to also be a paid escort, according to a series of Internet advertisements and a former Hollywood madam, Michelle Braun.

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Hollywood madam Michelle Braun provided tax returns to E! Network that purport to show her travel agency - a front for her escort service - paid Holly Sampson more than $24,000 in 2009. Braun also told the New York Daily News that Tiger Woods purchased her services.

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Woods has not commented on Sampson's claims or the claims of other alleged mistresses. On Dec. 2, Woods issued a statement on his Web site in which he apologized for "transgressions" without detailing them.

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Crimesider has discovered numerous advertisements posted to paid escort sites which feature photographs and what claim to be personal comments by Sampson. One ad claims Sampson will leave you "breathless."

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One undated advertisement on City-Source.com, an escort directory, has photographs of Holly Sampson both naked and semi-clothed and claims that Sampson is available for "Gentlemen with Discriminating Taste!" "When you want the finest wine, do you buy what's on sale?" the ad reads. "When you crave an amazing meal, do you settle for the $1 menu?"

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Holly Sampson is not the only woman to claim a sexual affair with Tiger Woods, whose background has legal implications. Los Angeles cocktail waitress Jaimee Grubbs, shown here, was arrested in San Diego for theft.

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Jaimee Grubbs was arrested, and spent a night in jail, in San Diego back in July 2004 for shoplifting a coat at a Nordstrom store.

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Grubbs pleaded guilty to misdemeanor grand theft in 2004 related to that shoplifting incident at a San Diego Nordstrom department store. According to court papers, obtained by ET Online, she completed an eight-hour theft program after pleading guilty.

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In 2007 and 2008, Capital One Bank filed court papers against Grubbs after she failed to pay a credit card balance of $868.07. According to the papers, obtained by ET Online, that figure grew to $1,353.93 including attorney fees, interest and more costs.

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Grubbs claims to have saved 300 text messages written by Tiger Woods during their alleged illicit relationship. Woods purportedly left a voicemail on Grubbs' cell phone on Nov. 24, 2009, three days before his middle-of-the-night car crash outside his home in Florida.

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In the voicemail she released, a man says to Grubbs: "Can you please, uh, take your name off your phone. My wife went through my phone. And, uh, may be calling you. If you can, please take your name off that and, um, and what do you call it just have it as a number on the voicemail, just have it as your telephone number. That's it, OK. You gotta do this for me. Huge. Quickly. All right. Bye."

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Tiger Woods has faced intense media scrutiny after a car accident outside his home early Friday, Nov. 27, 2009, and sordid allegations of affairs. In a 317-word statement on his Web site on Dec. 2, 2009, Woods acknowledged he had "let my family down and I regret those transgressions with all of my heart."

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The statement followed an Us Weekly cover story featuring Grubbs, who claimed she had a 31-month affair with Tiger Woods after meeting him at a Las Vegas nightclub the week after the 2007 Masters, two months before Woods' wife, Elin, gave birth to their first child.

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Jaimee Grubbs was arrested, and spent a night in jail, in San Diego back in July 2004 for shoplifting a coat at a Nordstrom store.

Credit: Personal Photo

Grubbs pleaded guilty to misdemeanor grand theft in 2004 related to that shoplifting incident at a San Diego Nordstrom department store. According to court papers, obtained by ET Online, she completed an eight-hour theft program after pleading guilty.